Azo dyestuffs



Patented Nov. 16, 1937 UNITED- STATES PATENT or ice "3,69 ,168 if L a 7 I AZO DYEsTUFFs U p v Max Albert Kunz, Mannheim, and Hans Krzikalla and Walter Limbacher, Ludwigshafen-on-the- Rhine, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application April 6, 1934, SerialNol" '719A04- In Germany April '13, 1933 3 Claims.

The-present invention relates to new azo dyestuffs and a process of producingrsame.

pound corresponding 7 to the formula wherein one X represents hydrogen and the other Xs hydrogemhalogen (preferably chlorine) or sulphonic acid, methyl, nitro or amino groups, the components being so selected that one sulphonic acid group is contained in the dyestuff'molecule.

In the preparation of the dyestuffs the procedure may be for example that an 8-hydroxyquinoline free from sulphonic acid groups is coupled with a diazotized halogenaminobenzene sulphonic acid free from hydroxy groups, or that a sulphonic acid of 8-hydroxyquinoline, as for example 8-hydroxyquinoline-5-sulphonic acid, is coupled with a diazotized halogenaminobenzene free from hydroxy groups and sulphonic acid groups. For example diazotized chlorbenzene-G-sulphonic acid may be coupled with S-hydroxyquinoline or 5- or 6-methyl-8- hydroxyquinoline, or diazotized 1-amino-2-chlorbenzene-5-sulphonic acid may be coupled with 5-chlor-8-hydroxyquinoline; on the otherhand G-methyl- 8 -hydroxyquinoline- 5 -sulphonic acid may be coupled with diazotized 1-amino-2,5-dichlorbenzene or 1-amino-3-chlorbenzene.

The dyestuifs thus obtainable yield, by after- .treatment of the dyeings on wool with bichromate or by dyeing on chrome-mordanted wool, very beautiful, usually orange, dyeings having excellent properties as regards fastness; the dyestuffs possess the special advantage of enabling the dyeing of wool from'baths containing neutral chromium salts, i. e. according to the so-called single bath chroming process; hereby in'the most cases especially valuabledyeings of good fastness properties are produced.

The following examples will further illustrate the nature of this invention but the inventionis notrestricted to these examples. The parts are by weight.

' V the so-called single bath process.

1-amino-3- Example 1 20.7 parts of 1-amino-3-chlorbenzene-6 sulphonic acid are jdiazotized in the usual manner 'and the resulting solution of the diazo compound is allowed to flow into a solution of 15.9 parts of 8-.hydroxyquin'oline1 in "hydrochloric; acid .The coupling is carried out to completion by adding an excess of sodium acetate. A dyestuff is obtained which yields uniform orange shades on wool; by aftertreatment of the dyeing with 'bichromate or by dyeing on chrome-mordanted wool the shade of color is only changed slightly and very fast orange dyeings are obtained. The dyestuff also dyes wool orange shades very well from a bath containing neutral chromium salts-- Dyestuffs of similar shades are obtained byemploying 1 -amino- 2 -chlorbenzene- 5 -sulphonic 1-amino-4-chlorbenzene-Z sulphonic acid instead acid, 1-amino-4-chlorbenzene-3-sulphonic acid or of 1-amino-3-chlorbenzene-6-sulphonic acid or by employing 5-methyl-8-hydroxyquinoline or .5- chlor-8-hydroxyquinoline as coupling compo,- nents.

Example 2 The diazo compound obtained from 24.1 parts of 1-amino-3,4-dichlorbenzene-fi-sulphonic acid is coupled with 15.9 parts of 8-hydroxyquinoline in a solution rendered alkaline with sodium carbonate. The resulting dyestuff yields orange dyeings on wool which by aftertreatmentwith bichromate give very fast orange shades such as may also be obtained by dyeing on chrome-mordanted wool.

' Example 3 The diazo compound prepared from 12.7 parts of l-amino 3-chlorbenzene is coupled with 24.7 parts of 8-hydroxyquinoline-5-sulphonic acid in a solution rendered alkaline with sodium carbonate. red shades; by aftertreatment of the dyeing with bichromate or by dyeing on chrome-mordanted wool fast orange dyeings are obtained.

7 Example 4 16.1 parts of 1 amino-2,5-dichlorbenzene are diazotized in the usual manner and the resulting solution -of the diazo compound is allowed to flow into a solution of 24.7 parts of 8'-hydroxyquinoline-5-sulphonic acid which has been rendered alkaline with sodium carbonate. A dye-. stuff is obtained which yields yellow-red dyeings on wool which by aftertreatment with bichromate The resulting dyestuff dyes wool yellowgive fast orange dyeings. The same shade is obtained by dyeing on chrome-mordanted wool.

Ewample 5 wherein the azo group is attached to one of the positions marked X, the remaining Xs being selected from the group consisting of hydrogen, halogen, methyl, nitro, amino and SO3H groups, and wherein Y is a member of the group consisting of hydrogen and. SOaI-I, the dyestuffs containing one SO3H group in their molecule.

2. The azo dyestufi corresponding to the formula 3. The azo dyestuff corresponding to the formula MAX ALBERT KUNZ. HANS KRZIKALLA. WALTER LIMIBACHER. 

